Role Overview

Block has transformed commerce since 2009, evolving from simple payment solutions to comprehensive omnichannel platforms that empower sellers of all sizes. Our integrated ecosystem includes point-of-sale hardware, e-commerce software, inventory management, buy-now-pay-later with Afterpay, staff management, and embedded financial services. As we expand aggressively in Canada, we're seeking a strategic leader to own GTM Strategy & Operations.

In this pivotal role, you'll bridge strategy and execution, partnering with Sales, Account Management, Partnerships, Marketing, Product, and Finance leaders. Your work will directly fuel revenue acceleration, market share gains, and sustainable growth. From developing vertical-specific playbooks to co-leading planning rhythms with Finance, you'll combine sharp analytical thinking with hands-on operational excellence to help Block dominate the Canadian commerce landscape.

This isn't just a job—it's a chance to build a lasting business impact at a company that's redefining how millions of sellers operate worldwide. Toronto's vibrant tech ecosystem and proximity to key verticals like retail, hospitality, and professional services make it the perfect hub for this role.

Key Responsibilities

The Canada GTM Strategy & Operations Lead owns the full spectrum of growth initiatives. Here's what you'll do daily:

• Transform market research, competitive intelligence, and customer data into actionable GTM strategies that drive revenue acceleration and market expansion.
• Prioritize opportunities across customer segments, making crisp trade-off recommendations and mobilizing cross-functional teams for execution.
• Design, launch, and scale repeatable playbooks for key verticals (retail, restaurants, services), channels, and strategic partnerships.
• Scope and lead high-impact strategic programs end-to-end, delivering measurable business outcomes.
• Build robust business cases, align diverse stakeholders, and ensure flawless execution of market launches.
• Co-lead annual planning, quarterly forecasting, and long-range strategy with Finance partners.
• Run disciplined rhythm-of-business (ROB) processes including monthly business reviews and performance deep dives.
• Define success KPIs in collaboration with Analytics and Finance, embedding them into team workflows.
• Track goal attainment, diagnose performance gaps, and drive rapid course corrections.
• Use data insights to guide resource allocation, double down on winners, and pivot from underperformers.
• Activate high-value partnerships and channel ecosystems to expand reach and revenue.
• Foster accountability and operational rigor across all GTM functions.

Qualifications

To succeed, you'll bring:

• 8+ years in GTM strategy, ops, or biz dev, ideally in fintech, payments, or SaaS.
• Proven revenue growth impact in competitive markets like Canada.
• Cross-functional leadership experience with Sales, Marketing, Product, Finance.
• Expertise in strategic planning and execution rhythms.
• Advanced data analysis and KPI management skills.
• Canadian market knowledge; payments/commerce experience a plus.
• Exceptional stakeholder influence and communication.
• Bachelor's degree; MBA preferred.
• Tool proficiency: Salesforce, Tableau, Google Analytics, financial modeling.
• Thrives in ambiguity with high ownership mindset.

Salary & Benefits

Competitive compensation package estimated at $140,000-$200,000 USD base (CAD equivalent), plus bonuses, equity, and comprehensive benefits including health coverage, unlimited PTO, professional development, parental leave, wellness stipends, and more. Full details provided during interview process.

Why Join Block?

Block is more than a fintech leader—we're building the future of commerce. Work with brilliant minds on products used by millions, enjoy Toronto's tech scene, and grow your career globally. Our culture emphasizes impact, ownership, and innovation. With Afterpay integration and expanding financial services, the growth trajectory is unmatched.

Benefits include equity upside, flexible work, learning stipends, and a mission-driven environment helping sellers thrive.

How to Apply

Ready to lead Canada's GTM acceleration? Submit your resume and cover letter highlighting GTM wins. We're moving fast—apply now to join Block's Toronto team and shape commerce tomorrow.